Methods for the production of polyolefins with end-functionalized groups are typically multi-step processes that often create unwanted by-products and waste of reactants and energy. For reviews of methods to form end-functionalized polyolefins, see: S. B. Amin and T. J. Marks, Angew. Chem. Int. Ed. 2008, 47, pp. 2006-2025; T. C. Chung, Prog. Polym. Sci. 2002, 27, pp. 39-85; and R. G. Lopez, F. D'Agosto, C. Boisson, Prog. Polym. Sci. 2007, 32, pp. 419-454. A process with a reduced number of steps would be desirable.
U.S. Pat. No. 4,110,377 discloses secondary aliphatic amines alkylated with alpha-olefins, such as ethylene, propylene, hexene, and undecene. Likewise, several literature references disclose hydroaminoalkylation of olefins using various catalysts (see J. Am. Chem. Soc. 2008, 130, pp. 14940-14941; J. Am. Chem. Soc. 2007, 129, pp. 6690-6691; Angew. Chem. Int. Ed. 2009, 48, pp. 8361-8365; Angew. Chem. Int. Ed. 2009, 48, pp. 4892-4894; Yuki Gosei Kagaku Kyokaishi (2009), 67(8), pp. 843-844; Angewandte Chemie, International Edition (2009), 48(6), pp. 1153-1156; Tetrahedron Letters (2003), 44(8), pp. 1679-1683; and Synthesis (1980), (4), pp. 305-306.
WO 98/33842 discloses the production of branched polyolefins comprising a silicon containing polymeric backbone with branches extending therefrom in which the branches are formed of polyolefins wherein the branched polymers are produced by a hydrosilation reaction between the polyolefin prearms with a hydrosilane containing group.
U.S. Pat. No. 6,084,030 discloses branched polyolefin polymers in the form of a comb, star, nanogel, and structural combinations thereof comprising a plurality of polyolefin arms selected from the group consisting of (1) polymers of ethylene; (2) polymers of propylene; and (3) copolymers of ethylene with one or more 1-alkenes, said arms being linked to the polymeric backbone, wherein the reactive polymeric backbone is formed from a siloxane, and said backbone contains at least 4-300 polyolefin arms, and said branched polyolefin polymer is prepared by coupling the polyolefin prearms with said polymeric backbone.
U.S. Pat. No. 8,399,725 discloses certain vinyl terminated oligomers and polymers that are functionalized for use in lubricant applications.
U.S. Pat. No. 8,372,930 discloses certain vinyl terminated oligomers and polymers that are functionalized in U.S. Pat. No. 8,399,725.
U.S. Pat. No. 8,283,419 discloses a process to functionalize propylene homo- or co-oligomer comprising contacting an alkene metathesis catalyst with a heteroatom containing alkene and a propylene homo- or co-oligomer having terminal unsaturation.
U.S. Pat. No. 8,501,894 discloses a process to functionalize polyolefins comprising contacting a metallocene catalyst with a hydrosilane, and one or more vinyl terminated polyolefins. This invention further relates to the hydrosilane-functionalized polyolefins produced thereby.
U.S. Publication No. 2012-0245293 discloses a process to functionalize polyolefins comprising contacting a metallocene catalyst with a difunctional diblock hydrosilane, and one or more vinyl terminated polyolefins. This invention further relates to the diblock hydrosilane-functionalized polyolefins produced thereby.
End-functionalized polyolefins that feature a chemically reactive or polar end group are of interest for use in a broad range of applications as compatibilizers, tie-layer modifiers, surfactants, and surface modifiers.
Thus, there is an ongoing need to develop a means to provide functionalized polyolefins with different polymeric architectures by efficient reactions, particularly reactions with good conversion, preferably under mild reaction conditions with a minimal number of steps, preferably one or two steps, preferably without solvent.